Skip to main content
Log in

Beckmann rearrangement of acetylthiophene oxime benzenesulfonates as a method for the synthesis of acetamidothiophenes

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The Beckmann rearrangement of 2-acetylthiophene, 5-methyl-2-acetylthiophene, 5-chloro-2-acetylthiophene, and 2,5-dichloro-3-acetylthiophene oxime benzenesulfonates to the corresponding acetamidothiophenes was carried out by heating with an aqueous methanol solution of sodium acetate. This method can be used for the preparative synthesis of 2-acetamidothiophene and 2,5-dichloro-3-acetamido-thiophene.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. O. Meth-Cohn, B. Tarnowski, and B. Narine, J. Chem. Soc., Perkin I, No. 5, 1531 (1981).

    Google Scholar 

  2. Ya. L. Gol'dfarb, M. M. Polonskaya, B. P. Fabrichnyi, and I. F. Shalavina, Dokl. Akad. Nauk SSSR, 126, 86 (1956).

    Google Scholar 

  3. L. N. Klemm and W. Hsin, J. Heterocycl. Chem., 12, 1183 (1975).

    Google Scholar 

  4. P. Claude and F. Outurquin, J. Heterocycl. Chem., 20, 113 (1983).

    Google Scholar 

  5. G. Ah-Kow, C. Paulmier, and P. Pastour, Bull. Soc. Chim. France, Part 2, 151 (1976).

    Google Scholar 

  6. D. Binder, G. Habison, and C. R. Noe, Synthesis, No. 4, 255 (1977).

    Google Scholar 

  7. I. L. Knunyants and B. P. Fabrichnyi, Reactions and Methods in the Investigation of Organic Compounds [in Russian], Vol. 3, Goskhimizdat, Moscow (1954), p. 139.

    Google Scholar 

  8. J. Cymerman-Craig and D. Willis, J. Chem. Soc., 1071 (1955).

  9. O. Meth-Cohn and B. Narine, Synthesis, No. 2, 133 (1980).

    Google Scholar 

  10. J. Cymerman-Craig and A. R. Naik, J. Am. Chem. Soc., 84, 3410 (1962).

    Google Scholar 

  11. B. P. Fabrichnyi, I. F. Shalavina, and Ya. L. Gol'dfarb, Zh. Obshch. Khim., 31, 1244 (1961).

    Google Scholar 

  12. A. Buzas and J. Teste, Bull. Soc. Chim. France, No. 2, 359 (1960).

    Google Scholar 

  13. B. P. Fabrichnyi, S. M. Kostrova, G.P. Gromova, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin., No. 11, 1483 (1973).

    Google Scholar 

  14. M. P. Chabrier, B. Tchoubar, and S. Le Tellier-Dupre, Bull. Soc. Chim. France, 13, 332 (1946).

    Google Scholar 

  15. J. Engel, A. Kleemann, F. Stroman, and K. Thiemer, West German Offenlegungsschrift, No. 2,851,387; Chem. Abstr., 91, 74,460 (1979).

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 483–485, April, 1985.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fabrichnyi, B.P., Bulgakova, V.N. & Gol'dfarb, Y.L. Beckmann rearrangement of acetylthiophene oxime benzenesulfonates as a method for the synthesis of acetamidothiophenes. Chem Heterocycl Compd 21, 401–403 (1985). https://doi.org/10.1007/BF00504398

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00504398

Keywords

Navigation